The proposed research involves the evaluation and follow-up of a new chemical reaction observed on the alkaloid, cocaine. The observed reaction is the demethylation of the tertiary nitrogen using 300-nm light in methanol solution. The conditions are mild and consequently this reaction has the potential of becoming a useful tool in alkaloid chemistry. All indications at present are that the benzoate group of cocaine absorbs the light and causes the reaction via some form of intramolecular process a hitherto unknown reaction. The experiments outlined herein will examine the nature of the light absorbing species which causes the reaction, how the interaction between the two groups is effected and the extension to the intermolecular reaction. We tentatively envision the demethylation reaction to be an imine formation and hydrolysis. Where the imine can, it will rearrange to form an enamine. The formation of enamines in this manner promises to even be a more useful reaction than the dealkylation one. An outline of the proposed work is as follow: 1. The nature of the light absorbing functional group; A. The solvent effect on the uv spectrum of cocaine; b. Substituting the phenylacetyl group for the benzoyl group on cocaine. 2. Evaluating the effect of various para-substituents on the benzoyl ring of cocaine; 3. The elimination of the carboxymethyl group; 4. The variation of the stereochemistry of C6 of cocaine; 5. The investigation of the intermolecular reaction between methyl benzoate and tertiary amines; 6. The effect of the amine on the formation of benzoic acid.